HCID 10199020, compound → (1R,2S,4R)-N-Boc-1-amino-2-hydroxycyclopentane-4-carboxylic acid methyl ester

Participants

Reaction Steps

[(1,2-Bis(2R,5R)-2,5-dimethylphospholano)benzene](cyclooctadiene)rhodium(I) tetrafluoroborate (23 mg, 1 mol %) was added to a degassed solution of (3S,4R)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester (1 g, 3.9 mmol) in methanol (5 ml). The reaction mixture was transferred to a bomb and, after purging with nitrogen and then hydrogen, a hydrogen pressure of 5 bar was applied and the reaction stirred for 14 h. The pressure was released and the bomb purged with nitrogen. Concentration of the reaction mixture gave a residue which was redissolved in dichloromethane (5 ml) Addition of silica (0.5 g) was stirring removed the catalyst from the reaction, and filtration and concentration of the organic solution gave the title compound as an off-white solid of 98% d.e. in quantitative yield.

Provenance & Evidence